4-Nitrotoluene → HCID 13115425, compound

HRID 1075321Notes

Reaction equation

HRID 1075321 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1)([O-:3])=[O:2].O[CH2:12][NH:13][C:14](=[O:16])[CH3:15].C(OCCCC)(=O)C>S(=O)(=O)(O)O>[CH3:10][C:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][C:6]=1[CH2:12][NH:13][C:14](=[O:16])[CH3:15]

Participants

5

Reactant 3

HCID 74734-NitrotolueneHCID 31272Butyl AcetateHCID 69365Formicin

Product 1

HCID 13115425HCID 13115425, compoundYield 38%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A solution of p-nitrotoluene (6.85 g; 0.05 mol) in concentrated sulfuric acid (60 ml) is cooled in an ice bath and N-(hydroxymethyl)acetamide (4.45 g; 0.05 mol) is added. The reaction mixture is stirred until a solution is obtained and then continuously stirred for 16 hours at 55° C. The mixture is then poured onto ice and the resulting precipitate is isolated. This solid material is extracted with 85 ml of butyl acetate on a steambath. Concentration of the butyl acetate solution with subsequent cooling gives 3.9 g (i.e., 38% yield) of product. The butyl acetate insoluble material (2.5 g) is methylene bis(4-nitro-o-toluene).

Workup

  1. customis obtained
  2. stirringcontinuously stirred for 16 hours at 55° C
  3. additionThe mixture is then poured onto ice
  4. customthe resulting precipitate is isolated
  5. extractionThis solid material is extracted with 85 ml of butyl acetate on a steambath
  6. temperatureConcentration of the butyl acetate solution with subsequent cooling
  7. customgives 3.9 g (i.e., 38% yield) of product

Sources & evidence

ORD record
ord-112c22084813411fb051db762a881653
Source dataset
uspto-grants-1983_07
Patent number
US04395577

Reaction notes

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